EP0199382B1 - Adoucissant liquide pour le linge - Google Patents

Adoucissant liquide pour le linge Download PDF

Info

Publication number
EP0199382B1
EP0199382B1 EP86200424A EP86200424A EP0199382B1 EP 0199382 B1 EP0199382 B1 EP 0199382B1 EP 86200424 A EP86200424 A EP 86200424A EP 86200424 A EP86200424 A EP 86200424A EP 0199382 B1 EP0199382 B1 EP 0199382B1
Authority
EP
European Patent Office
Prior art keywords
composition
component
group
formula
ppm
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP86200424A
Other languages
German (de)
English (en)
Other versions
EP0199382A3 (en
EP0199382A2 (fr
Inventor
Toan Trinh
Donald Marion Swartley
Errol Hoffman Wahl
Ronald Lee Hemingway
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to AT86200424T priority Critical patent/ATE53229T1/de
Publication of EP0199382A2 publication Critical patent/EP0199382A2/fr
Publication of EP0199382A3 publication Critical patent/EP0199382A3/en
Application granted granted Critical
Publication of EP0199382B1 publication Critical patent/EP0199382B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/645—Mixtures of compounds all of which are cationic

Definitions

  • This invention relates to compositions and methods for softening fabrics during the rinse cycle of home laundering operations. This is a widely used practice to impart to laundered fabrics a texture or hand that is smooth, pliable and fluffy to the touch (i.e., soft).
  • Fabric softening compositions have long been known in the art and are widely utilized by consumers during the rinse cycles of automatic laundry operations.
  • fabric softening refers to a process whereby a desirably soft hand and fluffy appearance are imparted to fabrics.
  • compositions containing cationic nitrogenous compounds in the form of quaternary ammonium salts and substituted imidazolinium salts having two long chain acyclic aliphatic hydrocarbon groups are commonly used to provide fabric softening benefits when used in laundry rinse operations (See, for example, U.S. Pat. Nos. 3,644,203, Lamberti et al., issued Feb. 22, 1972; and 4,426,299, Verbruggen, issued Jan. 17, 1984; also "Cationic Surface Active Agents as Fabric Softeners," R. R. Egan, Journal of the American Oil Chemists' Society, January 1978, pages 118-121; and "How to Choose Cationics for Fabric Softeners," J. A. Ackerman, Journal of the American Oil Chemists' Society, June 1983, pages 1166-1169).
  • Quaternary ammonium salts having only one long chain acyclic aliphatic hydrocarbon group are less commonly used because for the same chain length, compounds with two long alkyl chains were found to provide better softening performance than those having one long alkyl chain.
  • monostearyltrimethyl ammonium chloride such as monostearyltrimethyl ammonium chloride
  • Nonquaternary amide-amines Another class of nitrogenous materials that are sometimes used in fabric softening compositions are the nonquaternary amide-amines.
  • a commonly cited material is the reaction product of higher fatty acids with hydroxy alkyl alkylene diamines.
  • An example of these materials is the reaction product of higher fatty acids and hydroxyethylethylenediamine (See “Condensation Products from p-Hydroxyethylethylenediamine and Fatty Acids or Their Alkyl Esters and Their Application as Textile Softeners in Washing Agents," H. W. Eckert, Fette-Seifen-Anstrichstoff, September 1972, pages 527-533).
  • U.S. Pat. No. 3,904,533 Neiditch et al., issued Sept. 9, 1975, teaches a fabric conditioning formulation containing a fabric softening compound and a low temperature stabilizing agent which is a quaternary ammonium salt containing one to three short chain C 10 -C 14 alkyl groups; the fabric softening compound is selected from a group consisting of quaternary ammonium salts containing two or more long chain alkyl groups, the reaction product of fatty acids and hydroxalkyl alkylene diamine, and other cationic materials.
  • FR-A 2 391 312 describes an aqueous, liquid textile plastifier comprising the reaction product of di- alkylenetriamine and fatty acids, and a cationic nitrogenous salt having one 0 7 - 15 alkyl chain.
  • nonionic detergents also may have detrimental effect on the cationic fabric softeners, sometimes even more so than the anionic surfactants.
  • the problem of interference by carryover detergents may be overcome by very thoroughly rinsing the fabrics.
  • fabric softening compositions which perform well across major categories of detergents.
  • Current representatives of major detergent categories are TIDE@ (anionic detergents), WISK @ (anionic detergents rich in LAS (linear alkylate sulfonate) surfactant) and CONCENTRATED ALL@ (nonionic detergents).
  • compositions which have good softening performance across major categories of detergents are provided.
  • a further object of the invention is to develop a method to provide softness to laundry washed with those major categories of detergents.
  • the present invention relates to fabric softening compositions in liquid form for use in home laundry operations.
  • the present invention is based on the discovery of the synergistic softening activity of the present composition relative to the softening activity of its components, and on its superior softening performance relative to conventional fabric softening agents such as ditallowdimethylammonium chloride when these compositions are added to the rinse cycle after the laundry is washed using representative detergents, namely, anionic TIDE powdered detergent, anionic WISK liquid detergent which is rich in LAS surfactant, and nonionic CONCENTRATED ALL powdered detergent.
  • representative detergents namely, anionic TIDE powdered detergent, anionic WISK liquid detergent which is rich in LAS surfactant, and nonionic CONCENTRATED ALL powdered detergent.
  • a fabric softening composition in the form of an aqueous dispersion comprising from 3% to 35% by weight of a mixture comprising:
  • this invention provides a process of softening fabrics with the compositions defined above.
  • compositions containing a mixture of: (a) reaction products of C 16 -C 22 fatty acids with polyamines and (b) cationic nitrogenous salts having only one Gs-C22 acyclic aliphatic hydrocarbon group have synergistic softening performance relative to the softening performance of their components when these compositions are added to the rinse cycle after the laundry is washed using TIDE, WISK, or CONCENTRATED ALL detergents.
  • These compositions also have better softening performance in said detergents relative to conventional fabric softening agents such as ditallowdimethylammonium chloride (DTDMAC) and to a ternary composition containing the above binary mixture and DTDMAC, when used at the same total level of softening actives.
  • DTDMAC ditallowdimethylammonium chloride
  • compositions of the present invention contain two essential components: (a) the reaction products of C 16 -C 22 fatty acids with a polyamine selected from the group consisting of hydroxyalkylalkylenediamines and dialkylenetriamines and mixtures thereof, (b) cationic nitrogenous salts having only one acyclic aliphatic C 16 -C 22 hydrocarbon group, and optionally (c) cationic nitrogenous salts having two or more acyclic aliphatic C 15 -C 22 hydrocarbon groups.
  • the three components (a), (b) and (c) are each expressed as plural Markush terms. Such terms as used herein are both singular, as well als plural, unless otherwise specified.
  • the amount of fabric softening agent in the compositions of this invention is from 3% to 35%, prefer- aby from 4% to 27%, by weight of the composition.
  • the lower limits are amounts needed to contribute effective fabric softening performance when added to laundry rinse baths in the manner which is customary in home laundry practice.
  • the higher limits are suitable for concentrated products which provide the consumer with more economical usage due to a reduction of packaging and distributing costs.
  • the fabric softening composition comprises the following components:
  • Component I comprises the mixture of fabric softening actives.
  • An essential softening agent (active) of the present invention is the reaction products of C 16 -C 22 fatty acids with a polyamine selected from the group consisting of hydroxyalkylalkylenediamines and dialkylenetriamines and mixtures thereof. These reaction products are mixtures of several compounds in view of the multi-functional structure of the polyamines (see, for example, the publication by H. W. Eckert in Fette-Seifen-Anstrichstoff, cited above).
  • the preferred Component I(a) is a nitrogenous compound selected from the group consisting of the reaction product mixtures or some selected components of the mixtures. More specifically, the preferred Component I(a) is compounds selected from the group consisting of:
  • Component I(a)(i) is commercially available as Mazamideo 6, sold by Mazer Chemicals, or Ceranine@ HC, sold by Sandoz Colors & Chemicals; here the C 16 -C 22 fatty acids are hydrogenated tallow fatty acids and the hydroxyalkylalkylenediamine is N-2-hydroxyethylethylenediamine, and R 1 is an aliphatic Cis-C 17 hydrocarbon group, and R 2 and R 3 are divalent ethylene groups.
  • Component I(a)(ii) is stearic hydroxyethyl imidazoline wherein R 1 is an aliphatic C 17 hydrocarbon group, R 2 is a divalent ethylene group; this chemical is sold under the trade names of Alk- azine® ST by Alkaril Chemicals, Inc., or Schercozoline@ S by Scher Chemicals, Inc.
  • Component I(a)(iv) is N,N"-ditallowalkoyldiethylenetriamine where Ri is an aliphatic C 15 -C 17 hydrocarbon group and R 2 and R 3 are divalent ethylene groups.
  • Component l(a)(v) is 1-tallowamidoethyl-2-tallowimidazoline wherein R 1 is an aliphatic C 15 -C 17 hydrocarbon group and R 2 is a divalent ethylene group.
  • the Component l(a)(v) can also be first dispersed in a Bronstedt acid dispersing aid having a pKa value of not greater than 6; provided that the pH of the final composition is not greater than 8.
  • a Bronstedt acid dispersing aid having a pKa value of not greater than 6; provided that the pH of the final composition is not greater than 8.
  • Some preferred dispersing aids are formic acid, phosphoric acid, or methylsulfonic acid.
  • N,N"-ditallowalkoyldiethylenetriamine and 1-tallowethylamido-2-tallowimidazoline are reaction products of tallow fatty acids and diethylenetriamine, and are precursors of the cationic fabric softening agent methyl-1-tallowamidoethyl-2-tallowimidazolinium methylsulfate (see "Cationic Surface Active Agents as Fabric Softeners," R. R. Egan, Journal of the American Oil Chemicals' Society, January 1978, pages 118-121).
  • N,N " -ditallowalkoyldiethylenetriamine and 1-tallowamidoethyl-2-tallowimidazoline can be obtained from Sherex Chemical Company as experimental chemicals.
  • Methyl-1-tallowamidoethyl-2-tallow- imidazolinium methylsulfate is sold by Sherex Chemical Company under the trade name Varisoft® 475.
  • the preferred Component I(b) is a cationic nitrogenous salt containing one acyclic aliphatic C 16 -C 22 hydrocarbon group selected from the group consisting of:
  • Component I(b)(i) are the monoalkyltrimethylammonium salts such as monotallowtrimethylammonium chloride, mono(hydrogenated tallow)trimethylammonium chloride, palmityltrimethylammonium chloride and soyatrimethylammonium chloride, sold by Sherex Chemical Company under the trade names Adogen@ 471, Adogen 441, Adogen 444, and Adogen 415, respectively.
  • R 4 is an acyclic aliphatic C 16 -C 18 hydrocarbon group
  • R 5 and R 6 are methyl groups.
  • Mono(hydrogenated tallow)trimethylammonium chloride and monotallowtrimethylammonium chloride are preferred.
  • Component I(b)(i) are behenyltrimethylammonium chloride wherein R 4 is a C 22 hydrocarbon group and sold under the trade name Kemamine@ Q2803-C by Humko Chemical Division of Witco Chemical Corporation; soyadimethylethylammonium ethosulfate wherein R 4 is a C 16 -C 18 hydrocarbon group, Rs is a methyl group, R 6 is an ethyl group, and A is an ethylsulfate anion, sold under the trade name Jordaquat@ 1033 by Jordan Chemical Company; and methyl-bis(2-hydroxyethyl)octadecylammonium chloride wherein R 4 is a C 18 hydrocarbon group, R 5 is a 2-hydroxyethyl group and R 6 is a methyl group and available under the trade name Ethoquad®18/12 from Armak Company.
  • Component I(b)(iii) is 1-ethyl-1-(2-hydroxyethyl)-2-isoheptadecylimidazolinium ethylsulfate wherein R 1 is a C 17 hydrocarbon group, R 2 is an ethylene group, R 5 is an ethyl group, and A is an ethylsulfate anion. It is available from Mona Industries, Inc., under the trade name Monaquat@ ISIES..
  • a preferred composition contains Component I(a) at a level of from 50% to 90% by weight of Component I and Component I(b) at a level of from 10% to 50% by weight of Component I.
  • the Anion A e provides electrical neutrality.
  • the anion used to provide electrical neutrality in these salts is a halide, such as fluoride, chloride, bromide, or iodide.
  • other anions can be used, such as methylsulfate, ethylsulfate, hydroxide, acetate, formate, sulfate, carbonate, and the like. Chloride and methylsulfate are preferred herein as anion A.
  • the liquid carrier is selected from the group consisting of water and mixtures of the water and short chain C 1 -C 4 monohydric alcohols.
  • Water used can be distilled, deionized, or tap water. Mixtures of water and up to 15% of a short chain alcohol such as ethanol, propanol, isopropanol or butanol, and mixtures thereof, are also useful as the carrier liquid.
  • the preferred optional cationic nitrogenous salts having two or more acyclic aliphatic C 15 -C 22 hydrocarbon groups or one said group and an arylalkyl group are selected from the group consisting of:
  • Component I(c)(i) are the well-known dialkyldimethylammonium salts such as ditallowdimethylammonium chloride, ditallowdimethylammonium methylsulfate, di(hydrogenated tallow)dimethylammonium chloride, distearyldimethylammonium chloride, dibehenyldimethylammonium chloride. Di(hydrogenated tallow)dimethylammonium chloride and ditallowdimethylammonium chloride are preferred.
  • dialkyldimethylammonium salts examples include di-(hydrogenated tallow)dimethylammonium chloride (trade name Adogen 442), ditallowdimethylammonium chloride (trade name Adogen 470), distearyldimethylammonium chloride (trade name ArosurfR TA-100), all available from Sherex Chemical Company.
  • Dibehenyldimethylammonium chloride wherein R 4 is an acyclic aliphatic C 22 hydrocarbon group is sold under the trade name Kemamine Q-2802C by Humko Chemical Division of Witco Chemical Corporation.
  • Component I(c)(ii) are methylbis(tallowamidoethyl)(2-hydroxyethyl)ammonium methylsulfate and methylbis(hydrogenated tallowamidoethyl)(2-hydroxyethyl)ammonium methylsulfate wherein R 1 is an acyclic aliphatic C 15 -C 17 hydrocarbon group, R 2 is an ethylene group, Rs is a methyl group, R 9 is a hydroxyalkyl group and A is a methylsulfate anion; these materials are available from Sherex Chemical Company under the trade names Varisoft 222 and Varisoft 110, respectively.
  • Component I(c)(iv) is dimethylstearylbenzylammonium chloride wherein R 4 is an acyclic aliphatic C 18 hydrocarbon group, R s is a methyl group and A is a chloride anion, and is sold under the trade names Varisoft SDC by Sherex Chemical Company and Ammonyx R 490 by Onyx Chemical Company.
  • Component I(c)(v) are 1-methyl-1-tallowamidoethyl-2-tallowimidazolinium methylsulfate and 1-methyl-1-(hydrogenated tallowamidoethyl)-2-(hydrogenated tallow)imidazolinium methylsulfate wherein R 1 is an acyclic aliphatic Cis-Ci ? hydrocarbon group, R 2 is an ethylene group, R 5 is a methyl group and A is a chloride anion; they are sold under the trade names Varisoft 475 and Varisoft 445, respectively, by Sherex Chemical Company.
  • a preferred composition contains Component I(c) at a level of from 10% to 80% by weight of said Component I.
  • a more preferred composition also contains Component I(c) which is selected from the group consisting of: (i) di(hydrogenated) tallow)dimethylammonium chloride and (v) methyl-1-tallowamidoethyl-2- tallowimidazolinium methylsulfate; and mixtures thereof.
  • a preferred combination of ranges for Component I(a) is from 10% to 80% and for Component I(b) from 8% to 40% by weight of Component I.
  • Component I is preferably present at from 4% to 27% by weight of the total composition. More specifically, this composition is more preferred wherein Component I(a) is the reaction product of 2 moles of hydrogenated tallow fatty acids with 1 mole of N-2-hydroxyethylethylenediamine and is present at a level of from 10% to 70% by weight of Component I; and wherein Component I(b) is mono(hydrogenated tallow)trimethylammonium chloride present at a level of from 8% to 20% by weight of Component I; and wherein Component I(c) is selected from the group consisting of di(hydrogenated tallow)dimethylammonium chloride, ditallowdimethylammonium chloride and methyl-1-tal- lowamidoethyl-2-tallowimidazolinium methylsulfate, and mixtures thereof; said Component I(c) is present at a level of from 20% to 75% by weight of Component I; and wherein
  • Adjuvants can be added to the compositions herein for their known purposes.
  • Such adjuvants include, but are not limited to, viscosity control agents, perfumes, emulsifiers, preservatives, antioxidants, bacteriocides, fungicides, colorants, dyes, fluorescent dyes, brighteners, opacifiers, freeze- thaw control agents, shrinkage control agents, and agents to provide ease of ironing.
  • These adjuvants, if used, are added at their usual levels, generally each of up to 5% by weight of the composition.
  • Viscosity control agents can be organic or inorganic in nature.
  • organic viscosity modifiers are fatty acids and esters, fatty alcohols, and water-miscible solvents such as short chain alcohols.
  • inorganic viscosity control agents are water-soluble ionizable salts.
  • suitable salts are the halides of the group 1A and 11A metals of the Periodic Table of the Elements, e.g., calcium chloride, magnesium chloride, sodium chloride, potassium bromide, and lithium chloride. Calcium chloride is preferred.
  • the ionizable salts are particularly useful during the process of mixing the ingredients to make the compositions herein, and later to obtain the desired viscosity.
  • the amount of ionizable salts used depends on the amount of active ingredients used in the compositions and can be adjusted according to the desires of the formulator. Typical levels of salts used to control the composition viscosity are from 20 to 6,000 parts per million (ppm), preferably from 20 to 4,000 ppm by weight of the composition.
  • bacteriocides used in the compositions of this invention are glutaraldehyde, formaldehyde, 2-bromo-2-nitropropane-1,3-diol sold by Inolex Chemicals under the trade name Bronopol R , and a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazoline-3-one sold by Rohm and Haas Company under the trade name KathonR CG/ICP.
  • Typical levels of bacteriocides used in the present compositions are from 1 to 1,000 ppm by weight of the composition.
  • antioxidants examples include propyl gallate, available from Eastman Chemical Products, Inc., under the trade names Tenoxo PG and Tenox S-1, and butylated hydroxy toluene, available from UOP Process Division under the trade name Sustaneo BHT.
  • the present compositions may contain silicones to provide additional benefits such as ease of ironing and improved fabric feel.
  • the preferred silicones are polydimethylsiloxanes of viscosity of from 10- 4 m 2 S-1 to 10-1 m2 S-1, preferably from 2 x 10-4 m 2 S-1 to 6 x 10-2 m2 S- 1 . These silicones can be used as is, or can be conveniently added to the softener compositions in a preemulsified form which is obtainable directly from the suppliers.
  • silicones examples include 60% emulsion of polydimethylsiloxane (3,5 x 10-4 m 2 S-1) sold by Dow Corning Corporation under the trade name DOW CORNING@ 1157 Fluid and 50% emulsion of polydimethylsiloxane (10-2 m2 S-1) sold by General Electric Company under the trade name General Electric@ SM 2140 Silicones.
  • the optional silicone component can be used in an amount of from 0.1% to 6% by weight of the composition.
  • short chain alcohols such as ethanol and isopropanol which are present in the commercially available quaternary ammonium compounds used in the preparation of the present compositions.
  • the short chain alcohols are normally present at from 1% to 10% by weight of the composition.
  • a preferred composition contains from 0.2% to 2% of perfume, from 0% to 3% of polydimethylsiloxane, from 0% to 0.4% of calcium chloride, from 1 ppm to 1,000 ppm of bacteriocide, from 10 ppm to 100 ppm of dye, and from 0% to 10% of short chain alcohols, by weight of the total composition.
  • the pH of the compositions of this invention is generally adjusted to be in the range of from 3 to 8, preferably from 4 to 6. Adjustment of pH is normally carried out by including a small quantity of free acid in the formulation. Because no strong pH buffers are present, only small amounts of acid are required. Any acidic material can be used; its selection can be made by anyone skilled in the softener arts on the basis of cost, availability, safety, etc. Among the acids that can be used are hydrochloric, sulfuric, phosphoric, citric, maleic, and succinic. For the purposes of this invention, pH is measured by a glass electrode in full strength softening composition in comparison with a standard calomel reference electrode.
  • liquid fabric softening compositions of the present invention can be prepared by convenional methods.
  • a convenient and satisfactory method is to prepare the softening active premix at about 72-77 ° C, which is then added with stirring to the hot water seat.
  • Temperature-sensitive optional components can be added after the fabric softening composition is cooled to a lower temperature.
  • the liquid fabric softening compositions of this invention are used by adding to the rinse cycle of conventional home laundry operations.
  • rinse water has a temperature of from 5 ° C to 60 ° C.
  • concentration of the fabric softener actives of this invention is generally from 10 ppm to 200 ppm, preferably from 25 ppm to 100 ppm, by weight of the aqueous rinsing bath.
  • the present invention in its fabric softening method aspect comprises the steps of (1) washing fabrics in a conventional washing machine with a detergent composition; and (2) rinsing the fabrics in a bath which contains the above-described amounts of the fabric softeners; and (3) drying the fabrics.
  • the fabric softening composition is preferably added to the final rinse. Fabric drying can take place either in an automatic dryer or in the open air.
  • compositions I and V and their fabric softening performance evaluation as compared to their individual components as illustrated by Compositions II, III and IV, used at equivalent levels of actives, illustrate the benefits achieved by the utilization of the compositions and methods of this invention. These examples are illustrative of the invention herein and are not to be construed as limiting thereof.
  • Composition I is a composition of this invention and contains as fabric softening active a 39.2:60.8 mixture of mono(hydrogenated tallow)trimethylammonium chloride and the reaction product of 2 moles of fatty acids with 1 mole of N-2-hydroxyethylethylenediamine. It was prepared as follows:
  • Composition II contained the reaction product of 2 moles fatty acids with one mole of N-2-hydroxyethylethylenediamine as the sole fabric softening active ingredient and was prepared using the preparation procedure of Composition I above, with the exception that 7.25 parts of Mazamide 6 was used and no Adogen 441 was used. The amount of distilled water used was 92.71 parts.
  • Composition III contained mono(hydrogenated tallow)trimethylammonium chloride as the sole fabric softening active ingredient and was prepared using the preparation procedure of Composition I with the exception that 14.5 parts of Adogen 441 was used and no Mazamide 6 was used. The amount of distilled water used was 85.46 parts.
  • Composition IV contained di(hydrogenated tallow)dimethylammonium chloride as the sole fabric softening active ingredient and was prepared using the preparation procedure of Composition with the exception that 8.735 parts of di(hydrogenated tallow)dimethylammonium chloride [Adogen 448E, 83% active, containing about 5.8% by weight of mono(hydrogenated tallow)trimethylammonium chloride and 13% ethanol] was used instead of the mixture of Mazamide 6 and Adogen 441. The amount of water used was 91.225 parts. The unadjusted pH of the emulsion was about 4.5 and was adjusted to pH 6.1 by the addition of a small amount of a 20% aqueous solution of sodium hydroxide.
  • Composition V contained as fabric softening active a mixture of the reaction product of 2 moles fatty acids with 1 mole N-2-hydroxyethylethylene diamine, mono(hydrogenated tallow)trimethylammonium chloride and di(hydrogenated tallow)dimethylammonium chloride. It was prepared using the preparation procedure of Composition I using 1.25 parts of Mazamide 6, 1 part of Adogen 441, 6.625 parts of Adogen 448E and 91.085 parts of distilled water.
  • compositions I through V all have 7.25% of fabric softening active by weight of the total composition. These compositions are summarized below in Tables 1A and 1 B.
  • compositions were tested for their fabric softening performance by the following subjective evaluation method.
  • Representative laundry loads which each include 1 poly/cotton shirt, 1 polyester blouse, 1 pair of polyester trousers, 1 pair of poly/cotton denims, 1 poly/cotton tee shirt, 2 cotton tee shirts, 1 nylon slip, 1 pair of nylon socks, 3 cotton bath towels, 2 poly/cotton pillow cases, and 8 cotton terry towelling test cloths were washed in a Kenmore R Heavy -Duty Automatic Washer Model 110 with a selected detergent at its recommended usage.
  • the amount of water used is about 75.7 liters, water hardness is about 0.12 g/I (7 grains/gallon), wash water temperature is about 38 ° C and rinse water temperature is about 18-21°C.
  • test terry cloths After the wash water was removed (spun out) and before the rinse water and the fabric softening composition were added, the 8 test terry cloths were collected, then 4 of them were tucked (unexposed) inside the laundry bundle and the remaining 4 were placed on top (exposed) of the laundry bundle. After drying, the "exposed" test terry cloths of one treatment were compared with the "exposed" terry cloths of the other treatment for softness, and likewise for the "unexposed” terry cloths. The overall relative rating was the average of these two comparison results for the "exposed" and "unexposed” terry cloths.
  • the softening performance of the binary Composition I and the ternary Composition V were compared with that of the single-component Compositions (II-IV).
  • Table 2 shows the results of the fabric softening composition treatments after the laundry loads were washed in TIDE, a granular heavy duty laundry detergent in which the surfactant is primarily of the anionic type; WISK, a liquid heavy duty laundry detergent in which the surfactant is primarily of the anionic type; and CONCENTRATED ALL, a granular heavy duty laundry detergent in which the surfactant is of a nonionic type.
  • TIDE a granular heavy duty laundry detergent in which the surfactant is primarily of the anionic type
  • WISK a liquid heavy duty laundry detergent in which the surfactant is primarily of the anionic type
  • CONCENTRATED ALL a granular heavy duty laundry detergent in which the surfactant is of a nonionic type.
  • a positive PSU value indicates that the test cloths treated with the composition on the left-hand side were
  • the binary Composition I of the present invention shows a synergistic softening activity across the detergent types when compared with the two individual materials making up the compositions (namely, Compositions II and III), as well as having better softening performance when compared with the DTDMAC Composition IV and the ternary composition containing Mazamide 6, MTT-MAC and DTDMAC (Composition V). It also can be seen that the ternary composition (Composition V) also has superior performance relative to its components (Compositions II-IV) across the detergent types, and is also a preferred composition of the present invention.
  • compositions VI to VIII in Table 3A and Compositions IX to XI in Table 3B are within the scope of this invention and are prepared by the same general procedure set forth for Composition I, hereinabove. These examples are provided herein for purposes of illustration only and are not intended to limit the claims.
  • compositions VI to VIII have fabric softening active levels in the conventional ranges while Compositions IX to XI are concentrated compositions having high levels of softening actives. Compositions VI to XI have good fabric softening performance across detergent types.
  • Composition XII was made by the following high shear milling process: 200 parts of Mazamide 6, 26 parts of predried Adogen 441 (97% active), 522 parts of Adogen 448E, 111 parts of methyl-1-tallowami- doethyl-2-tallowimidazolinium methylsulfate [Varisoft 475, 90% active and 10% isopropanol], and 25 parts of blue dye solution (1.35% active) were weighed into a premix vessel. This premix was melted, mixed and heated to 77 ° C. Two parts of Kathon CG/ICP were then added to the premix.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Ultra Sonic Daignosis Equipment (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Claims (21)

1. Composition aqueuse adoucissante pour tissus, comprenant les constituants suivants:
I. de 3% à 35%, en poids de la composition, d'un mélange comprenant:
(a) de 10% à 92% du produit de réaction d'acides gras en C16-C22 avec une polyamine choisie dans le groupe constitué par les hydroxyalkylalkylènediamines et les dialkylènetriamines et leurs mélanges;
(b) de 8% à 90% de sels azotés cationiques ne comportant qu'un groupe hydrocarboné aliphatique acyclique en C16-C22; et
(c) de 0% à 80% de sels azotés cationiques comportant deux groupes hydrocarbonés aliphatiques acycliques en C15-C22 ou plus, ou un de ces groupes et un groupe arylalkyle;
le tout en poids du constituant I;
Il. le reste de la composition comprenant un véhicule liquide choisi dans le groupe constitué par l'eau et les mélanges d'eau et de monoalcools en C1-C4.
2. Composition selon la revendication 1, dans laquelle ledit constituant I(a) est un composé azoté choisi dans le groupe constitué par:
(i) le produit de réaction d'acides gras en C16-C22 avec des hydroxyalkylalkylènediamines, dans un rapport moléculaire de 2:1, ledit produit de réaction contenant une composition renfermant un composé de formule:
Figure imgb0059
dans laquelle Ri est un groupe hydrocarboné aliphatique acyclique en C15-C21 et R2 et R3 sont des groupes alkylène divalents en C1-C3;
(ii) les composés imidazolines substitués de formule
Figure imgb0060
dans laquelle R1 et R2 sont tels que définis ci-dessus;
(iii) les composés imidazolines substitués de formule
Figure imgb0061
dans laquelle R1 et R2 sont tels que définis ci-dessus;
(iv) le produit de réaction d'acides gras en C16-C22 avec des dialkylènetriamines, dans un rapport moléculaire de 2:1, ledit produit de réaction contenant une composition renfermant un composé de formule:
Figure imgb0062
dans laquelle R1, R2 et R3 sont tels que définis ci-dessus; et
(v) les composés imidazolines substitués de formule
Figure imgb0063
dans laquelle R1 et R2 sont tels que définis ci-dessus; et leurs mélanges.
3. Composition selon la revendication 1, dans laquelle ledit constituant I(b) est un sel azoté cationique contenant un groupe hydrocarboné aliphatique acyclique en C16-C22, choisi dans le groupe constitué par:
(i) les sels d'ammonium quaternaire acycliques de formule:
Figure imgb0064
dans laquelle R4 est un groupe hydrocarboné aliphatique acyclique en C16-C22, Rs et R6 sont des groupes alkyle ou hydroxyalkyle saturés en C1-C4, et Ae est un anion;
(ii) les sels d'imidazolinium substitués de formule:
Figure imgb0065
dans laquelle Ri est un groupe hydrocarboné aliphatique acyclique en C16-C21, R7 est un hydrogène ou un groupe alkyle ou hydroxyalkyle saturé en Ci-C4, et Ae est un anion;
(iii) les sels d'imidazolinium substitués de formule:
Figure imgb0066
dans laquelle R2 est un groupe alkylène divalent en C1-C3 et Ri, Rs et Ae sont tels que définis ci-dessus;
(iv) les sels d'alkylpyridinium de formule:
Figure imgb0067
dans laquelle R4 est un groupe hydrocarboné aliphatique acyclique en C6-C22 et Ae est un anion; et
(v) les sels d'alcanamide-alkylène-pyridinium de formule:
Figure imgb0068
dans laquelle R1 est un groupe hydrocarboné aliphatique acyclique en C16-C21 et R2 est un groupe alkylène divalent en C1-C3, et Aθ est un anion; et leurs mélanges.
4. Composition selon la revendication 1, 2 ou 3, dans laquelle ledit constituant I(a) est présent en une proportion de 50% à 90% en poids du constituant I et ledit constituant I(b) est présent en une proportion de 10% à 50% en poids du constituant I.
5. Composition selon la revendication 4, dans laquelle ledit constituant I(a) est le produit de réaction de deux moles d'acides gras de suif hydrogéné avec une mole de N-2-hydroxyéthyléthylènediamine.
6. Composition selon la revendication 4, dans laquelle ledit constituant I(a) est le composé imidazoline substitué de formule:
Figure imgb0069
dans laquelle R1 est un groupe hydrocarboné aliphatique acyclique en C15-C17.
7. Composition selon la revendication 2, dans laquelle ladite composition comprend ledit constituant I(a)(v) et dans laquelle ledit constituant I(a)(v) est dispersé dans un auxiliaire de dispersion choisi dans le groupe des acides de Bronstedt ayant un pKa non supérieur à 6; à condition que le pH de la composition final ne soit pas supérieur à 8.
8. Composition selon la revendication 7, dans laquelle l'auxiliaire de dispersion est l'acide formique, l'acide phosphorique ou l'acide méthylsulfonique.
9. Composition selon la revendication 4, dans laquelle ledit constituant I(b) est le sel d'ammonium quaternaire acyclique de formule:
Figure imgb0070
dans laquelle R4 est un groupe hydrocarboné aliphatique acyclique en C16-C22.
10. Composition selon la revendication 4, dans laquelle ladite composition renferme de 0,2% à 2% de parfum, de 0% à 3% de polydiméthylsiloxane, de 1 ppm à 1000 ppm de bactéricide, de 20 ppm à 100 ppm d'un antioxydant, de 10 ppm à 100 ppm de colorant et de 0% à 10% d'alcools à chaîne courte, en poids de la composition.
11. Composition selon la revendication 1, 2 ou 3, dans laquelle ledit constituant I(c) est présent à raison de 10% à 80% en poids dudit constituant I.
12. Composition selon la revendication 11, dans laquelle ledit constituant I(c) est choisi dans le groupe constitué par:
(i) les sels d'ammonium quaternaire acycliques de formule:
Figure imgb0071
dans laquelle R4 est un groupe hydrocarboné aliphatique acyclique en C15-C22, Rs est un groupe alkyle ou hydroxyalkyle saturé en C1-C4, Re est choisi dans le groupe constitué par les groupes R4 et Rs, et A⊖ est un anion;
(ii) les sels de diamido-ammonium quaternaire de formule:
Figure imgb0072
dans laquelle R1 est un groupe hydrocarboné aliphatique acyclique en C15-C21, R2 est un groupe alkylène divalent comportant 1 à 3 atomes de carbone, R5 et R9 sont des groupes alkyle ou hydroxyalkyle saturés en C1-C4, et Ae est un anion;
(iii) les sels d'ammonium quaternaire diamino-alcoxylés de formule:
Figure imgb0073
dans laquelle n est égal à 1 à 5, et R1, R2, Rs et Ae sont tels que définis ci-dessus;
(iv) les composés d'ammonium quaternaire de formule:
Figure imgb0074
dans laquelle R4 est un groupe hydrocarboné aliphatique acyclique en C15-C22, Rs est un groupe alkyle ou hydroxyalkyle saturé en Ci-C4, Ae est un anion;
(v) les sels d'imidazolinium substitués de formule:
Figure imgb0075
dans laquelle Ri est un groupe hydrocarboné aliphatique acyclique en C15-C21, R2 est un groupe alkylène divalent comportant 1 à 3 atomes de carbone, et R5 et Ae sont tels que définis ci-dessus; et
(vi) les sels d'imidazolinium substitués de formule:
Figure imgb0076
dans laquelle Ri, R2 et Ae sont tels que définis ci-dessus; et leurs mélanges.
13. Composition selon la revendication 11, dans laquelle ledit constituant I(c) est choisi dans le groupe constitué par le chlorure de di(suif hydrogéné)-diméthyl-ammonium, le chlorure de disuif-diméthyl-ammonium et le méthylsulfate de méthyl-1-suifamidoéthyl-2-suifimidazolinium; et leurs mélanges.
14. Composition selon la revendication 11, dans laquelle ledit constituant I(a) est présent à raison de 10% à 80% et ledit constituant I(b) est présent à raison de 8% à 40% en poids du constituant I.
15. Composition selon la revendication 14, dans laquelle ledit constituant I est présent à raison de 4% à 27% en poids de la composition totale.
16. Composition selon la revendication 15, dans laquelle ledit constituant I(a) est le produit de réaction de 2 moles d'acides gras de suif hydrogéné avec environ 1 mole de N-2-hydroxyéthyléthylènediamine et est présent à raison de 10% à 70%; ledit constituant I(b) est du chlorure de mono(suif hydrogéné)-trimé- thyl-ammonium présent à raison de 8% à 20%; et ledit constituant I(c) est du chlorure de di(suif hydrogéné)-diméthyl-ammonium et est présent à raison de 20% à 75% en poids du constituant I.
17. Composition selon la revendication 15, dans laquelle ledit constituant I(c) est un mélange de chlorure de di(suif hydrogéné)-diméthyl-ammonium et de méthylsulfate de méthyl-1-suifamidoéthyl-2-suifimid- azolinium, présent à raison de 20% à 75% en poids du constituant I.
18. Composition selon la revendication 17, dans laquelle le rapport pondéral dudit chlorure de di(suif hydrogéné)-diméthyl-ammonium audit méthylsulfate de méthyl-1-suifamidoéthyl-2-suifimidazolinium est de 2:1 à 6:1.
19. Composition selon la revendication 14, comprenant en outre de 0,2% à 2% de parfum, de 0% à 3% de polydiméthylsiloxane, de 0% à 0,4% de chlorure de calcium, de 20 ppm à 100 ppm d'un antioxydant, de 1 ppm à 1000 ppm de bactéricide, de 10 ppm à 100 ppm de colorant et de 0% à 10% d'alcools à chaîne courte, en poids de la composition totale.
20. Procédé d'adoucissement de tissus comprenant (1) le lavage desdits tissus avec une composition détergente et (2) le rinçage des tissus dans un bain contenant une quantité efficace d'une composition adoucissante pour tissus comprenant les constituants suivants:
I. de 3% à 35%, en poids de la composition, d'un mélange comprenant:
(a) de 10% à 92% du produit de réaction d'acides gras en C16-C22 avec une polyamine choisie dans le groupe constitué par les hydroxyalkylalkylènediamines- et les dialkylènetriamines et leurs mélanges;
(b) de 8% à 90% de sels azotés cationiques ne comportant qu'un groupe hydrocarboné aliphatique acyclique en C16-C22; et
(c) de 0% à 80% de sels azotés cationiques comportant deux groupes hydrocarbonés aliphatiques acycliques en C15-C22 ou plus, ou un de ces groupes et un groupe arylalkyle; le tout en poids du constituant 1;
II. le reste de la composition comprenant un véhicule liquide choisi dans le groupe constitué par l'eau et les mélanges d'eau et de monoalcools en C1-C4; et dans lequel ledit bain de rinçage contient de 10 ppm à 200 ppm dudit mélange adoucissant pour tissus.
21. Procédé selon la revendication 20, dans lequel ledit bain de rinçage contient de 25 ppm à 100 ppm dudit mélange adoucissant pour tissus.
EP86200424A 1985-03-28 1986-03-18 Adoucissant liquide pour le linge Expired - Lifetime EP0199382B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT86200424T ATE53229T1 (de) 1985-03-28 1986-03-18 Fluessiger waescheweichmacher.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/717,051 US4661269A (en) 1985-03-28 1985-03-28 Liquid fabric softener
US717051 1985-03-28

Publications (3)

Publication Number Publication Date
EP0199382A2 EP0199382A2 (fr) 1986-10-29
EP0199382A3 EP0199382A3 (en) 1987-12-02
EP0199382B1 true EP0199382B1 (fr) 1990-05-30

Family

ID=24880512

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86200424A Expired - Lifetime EP0199382B1 (fr) 1985-03-28 1986-03-18 Adoucissant liquide pour le linge

Country Status (16)

Country Link
US (1) US4661269A (fr)
EP (1) EP0199382B1 (fr)
JP (1) JPS61275475A (fr)
KR (1) KR930004515B1 (fr)
AT (1) ATE53229T1 (fr)
AU (1) AU577009B2 (fr)
CA (1) CA1260654A (fr)
DE (1) DE3671644D1 (fr)
DK (1) DK139786A (fr)
FI (1) FI80904C (fr)
GB (1) GB2174423B (fr)
GR (1) GR860814B (fr)
HK (1) HK48892A (fr)
IE (1) IE58593B1 (fr)
MX (1) MX162681A (fr)
SG (1) SG49392G (fr)

Families Citing this family (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8520803D0 (en) * 1985-08-20 1985-09-25 Procter & Gamble Textile treatment compositions
GB8508129D0 (en) * 1985-03-28 1985-05-01 Procter & Gamble Ltd Textile treatment composition
US4728337A (en) * 1985-11-08 1988-03-01 Ciba-Geigy Corporation Assistant combination and use thereof as wool textile finishing agent
US4770815A (en) * 1986-10-24 1988-09-13 The Procter & Gamble Company Detergent plus softener with imidazoline ingredient
US5019280A (en) * 1986-11-14 1991-05-28 The Procter & Gamble Company Ion-pair complex conditioning agent with benzene sulfonate/alkyl benzene sulfonate anionic component and compositions containing same
US4772404A (en) * 1986-12-24 1988-09-20 Lever Brothers Company Concentrated liquid fabric softener with whiteners
US4756850A (en) * 1987-06-10 1988-07-12 The Procter & Gamble Company Articles and methods for treating fabrics
WO1988010294A1 (fr) * 1987-06-16 1988-12-29 Cotelle S.A. Compositions adoucissantes concentrees
US4800026A (en) * 1987-06-22 1989-01-24 The Procter & Gamble Company Curable amine functional silicone for fabric wrinkle reduction
US4822499A (en) * 1987-08-17 1989-04-18 The Procter & Gamble Company Liquid fabric softener with stable non-staining pink color
US4851139A (en) * 1987-08-26 1989-07-25 The Clorox Company Isotropic fabric softener composition containing fabric mildewstat
DE3877910T2 (de) * 1987-11-19 1993-05-19 British Petroleum Co Konditionierungsmittel fuer textilmaterialien.
US5013846A (en) * 1988-01-27 1991-05-07 The Procter & Gamble Company Process for preparing substituted imidazoline fabric conditioning compounds
EP0326213B1 (fr) * 1988-01-28 1994-11-09 Unilever N.V. Composition pour le traitement de matériaux textiles et sa préparation
US4857213A (en) * 1988-02-08 1989-08-15 The Procter & Gamble Company Liquid detergent containing conditioning agent and high levels of alkyl sulfate/alkyl ethoxylated sulfate
US5073274A (en) * 1988-02-08 1991-12-17 The Procter & Gamble Co. Liquid detergent containing conditioning agent and high levels of alkyl sulfate/alkyl ethoxylated sulfate
US4861502A (en) * 1988-02-08 1989-08-29 The Procter & Gamble Company Conditioning agent containing amine ion-pair complexes and composiitons thereof
US4840738A (en) * 1988-02-25 1989-06-20 The Procter & Gamble Company Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts
GB8805837D0 (en) * 1988-03-11 1988-04-13 Unilever Plc Fabric conditioning composition
US4844820A (en) * 1988-03-15 1989-07-04 The Procter & Gamble Company Liquid fabric softener comprising light-unstable red dye in protective package
US4863620A (en) * 1988-10-18 1989-09-05 The Procter & Gamble Company Acidic liquid fabric softener with yellow color that changes to blue upon dilution
US4897208A (en) * 1988-10-31 1990-01-30 The Procter & Gamble Company Liquid fabric softener colored pink
JPH02139480A (ja) * 1988-11-21 1990-05-29 Kao Corp 柔軟仕上剤
DE3842057A1 (de) * 1988-12-14 1990-06-28 Henkel Kgaa Textile weichmacher fuer flotten mit hohen gehalten an elektrolyten und/oder optischen aufhellern
US4994193A (en) * 1988-12-15 1991-02-19 The Procter & Gamble Company Liquid fabric softener
US4970008A (en) * 1988-12-20 1990-11-13 Kandathil Thomas V Fabric conditioner comprising a mixture of quaternary ammonium compounds and select tertiary amines
US5154841A (en) * 1988-12-21 1992-10-13 The Procter & Gamble Company Process for preparing substituted imidazoline fabric conditioning compounds
CA2016423C (fr) * 1989-05-19 1997-04-22 Toan Trinh Compositions de rincage pour le conditionnement des tissus, renfermant des agents assouplissants et des polymeres de polyester cationique antisalisseurs
US5116520A (en) * 1989-09-06 1992-05-26 The Procter & Gamble Co. Fabric softening and anti-static compositions containing a quaternized di-substituted imidazoline ester fabric softening compound with a nonionic fabric softening compound
NZ235490A (en) * 1989-10-16 1993-08-26 Colgate Palmolive Co Fabric-softening compositions
US4976878A (en) * 1990-01-18 1990-12-11 The Procter & Gamble Company Process for recovering gelled aqueous liquid fabric softener
ZA914152B (en) * 1990-06-01 1993-01-27 Unilever Plc Liquid fabric conditioner and dryer sheet fabric conditioner containing fabric softener,aminosilicone and bronsted acid compatibiliser
US5174911A (en) * 1990-06-01 1992-12-29 Lever Brothers Company, Division Of Conopco, Inc. Dryer sheet fabric conditioner containing compatible silicones
US5064544A (en) * 1990-06-01 1991-11-12 Lever Brothers Company, Division Of Conopco, Inc. Liquid fabric conditioner containing compatible amino alkyl silicones
JPH0441776A (ja) * 1990-06-01 1992-02-12 Kao Corp 液体柔軟仕上剤
JPH0768669B2 (ja) * 1990-10-05 1995-07-26 花王株式会社 濃縮型柔軟仕上剤
US5484540A (en) * 1991-03-08 1996-01-16 The Procter & Gamble Company Concentrated fabric softening compositions
WO1992019714A1 (fr) * 1991-04-30 1992-11-12 The Procter & Gamble Company Produits assouplissants contenant de l'imidazoline substituee et des composes fortement ethoxyles
EP0536444A1 (fr) * 1991-10-07 1993-04-14 The Procter & Gamble Company Emulsion de parfum stable et concentrée
US5254269A (en) * 1991-11-26 1993-10-19 Lever Brothers Company, Division Of Conopco, Inc. Fabric conditioning composition containing an emulsified silicone mixture
AU673079B2 (en) * 1993-07-15 1996-10-24 Colgate-Palmolive Company, The Concentrated liquid fabric softening composition
US5616553A (en) * 1993-08-12 1997-04-01 The Procter & Gamble Company Fabric conditioning compositions
US5599786A (en) * 1993-08-12 1997-02-04 The Procter & Gamble Company Cellulase fabric-conditioning compositions
US5670472A (en) * 1994-04-19 1997-09-23 Witco Corporation Biodegradable ester diquaternary compounds and compositions containing them
CZ311096A3 (en) * 1994-04-29 1997-05-14 Procter & Gamble Cellulose preparations for conditioning fabrics
US5445747A (en) * 1994-08-05 1995-08-29 The Procter & Gamble Company Cellulase fabric-conditioning compositions
JP3475596B2 (ja) * 1995-08-01 2003-12-08 チッソ株式会社 耐久親水性繊維、布状物及び成形体
ATE321574T1 (de) 1995-08-31 2006-04-15 Procter & Gamble Verwendung von allylalkohol als ein mittel zur verminderung von schlechten gerüchen
DE69526439T2 (de) 1995-09-18 2002-12-12 Procter & Gamble Stabilisierte Textilweichmacherzusammensetzungen
CA2250225A1 (fr) * 1996-03-29 1997-10-09 Frederick Anthony Hartman Utilisation d'une composition d'adoucissant pour textiles
US6025321A (en) * 1996-03-29 2000-02-15 The Procter & Gamble Company Dryer-added fabric softener composition to provide color and other fabric benefits in package in association with instructions for use
ATE235544T1 (de) 1996-10-30 2003-04-15 Procter & Gamble Gewebeweichmacherzusammensetzungen
US5919750A (en) * 1997-07-24 1999-07-06 Akzo Nobel Nv Fabric softener composition
US6630441B2 (en) * 1997-07-29 2003-10-07 The Procter & Gamble Company Concentrated, stable, preferably clear, fabric softening composition containing amine fabric softener
EP0990695A1 (fr) * 1998-09-30 2000-04-05 Witco Surfactants GmbH Composition adoucissante inhibitant le transfert de colorants
US6818610B2 (en) * 2001-07-27 2004-11-16 Procter & Gamble Company Fabric care systems for providing anti-wrinkle benefits to fabric
US7980001B2 (en) * 2004-02-27 2011-07-19 The Procter & Gamble Company Fabric conditioning dispenser and methods of use
US7304027B1 (en) 2006-07-31 2007-12-04 The Dial Corporation Phase-stable concentrated fabric softeners containing borates
DE102007012910A1 (de) 2007-03-19 2008-09-25 Momentive Performance Materials Gmbh Mit Duftstoffen modifizierte, verzweigte Polyorganosiloxane
DE102007012909A1 (de) 2007-03-19 2008-09-25 Momentive Performance Materials Gmbh Mit Duftstoffen modifizierte, reaktive Polyorganosiloxane
EP2158352B1 (fr) 2007-06-15 2017-12-20 Ecolab Inc. Methode d'utilisation d'une composition assouplissante pour textile liquide
MX2011004745A (es) * 2008-11-26 2011-05-24 Colgate Palmolive Co Composiciones y metodos suavizantes de telas.
EP3134499A4 (fr) 2014-04-23 2018-02-28 Steinemann, Anne Formulations de nettoyage pour des individus sensibles aux produits chimiques : compositions et procédés
US9725679B2 (en) 2014-11-21 2017-08-08 Ecolab Usa Inc. Compositions to boost fabric softener performance
US9506015B2 (en) 2014-11-21 2016-11-29 Ecolab Usa Inc. Compositions to boost fabric softener performance
US9688945B2 (en) 2014-11-21 2017-06-27 Ecolab Usa Inc. Compositions to boost fabric softener performance
KR20170105074A (ko) 2015-01-14 2017-09-18 그레고리 반 버스커크 얼룩 방출을 위한 개선된 직물 처리방법
US10975338B2 (en) 2017-05-16 2021-04-13 The Procter & Gamble Company Active agent-containing three-dimensional articles
US10975340B2 (en) 2017-05-16 2021-04-13 The Procter & Gamble Company Active agent-containing fibrous structure articles
US10975339B2 (en) 2017-05-16 2021-04-13 The Procter & Gamble Company Active agent-containing articles
US20230092174A1 (en) 2021-08-02 2023-03-23 The Procter & Gamble Company Active agent-containing articles

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2391312A1 (fr) * 1977-05-16 1978-12-15 Basf Ag Plastifiant textile aqueux liquide

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK131432A (fr) * 1968-12-09
DE1922047C3 (de) * 1969-04-30 1978-03-30 Henkel Kgaa, 4000 Duesseldorf Nachspülmittel für gewaschene Wäsche
CH592163A5 (fr) * 1973-10-16 1977-10-14 Alusuisse
US3974076A (en) * 1974-01-11 1976-08-10 The Procter & Gamble Company Fabric softener
NL7609621A (nl) * 1975-09-04 1977-03-08 Hoechst Ag Textielbehandelingsmiddel.
CH646742A5 (de) * 1977-07-06 1984-12-14 Procter & Gamble Konzentrierte fluessige weichmacherzusammensetzung.
US4327133A (en) * 1977-11-21 1982-04-27 Lever Brothers Company Additives for clothes dryers
EP0013780B2 (fr) * 1979-01-11 1988-08-31 THE PROCTER & GAMBLE COMPANY Composition concentrée d'adoucissement pour tissus
DE2925859A1 (de) * 1979-06-27 1981-01-22 Henkel Kgaa Waeschenachbehandlungsmittel
EP0032267A1 (fr) * 1980-01-11 1981-07-22 THE PROCTER & GAMBLE COMPANY Compositions concentrées de traitement de textiles et procédé pour leur préparation
US4421792A (en) * 1980-06-20 1983-12-20 Lever Brothers Company Additives for clothes dryers
US4399045A (en) * 1980-11-18 1983-08-16 The Procter & Gamble Company Concentrated fabric softening compositions
DE3129549A1 (de) * 1981-07-27 1983-02-10 Henkel KGaA, 4000 Düsseldorf Mittel zum nachbehandeln gewaschener waesche in einem waeschetrockner
US4439335A (en) * 1981-11-17 1984-03-27 The Procter & Gamble Company Concentrated fabric softening compositions
US4464272A (en) * 1982-02-10 1984-08-07 Lever Brothers Company Fabric softening composition
DE3309569A1 (de) * 1982-03-22 1983-10-27 Colgate-Palmolive Co., 10022 New York, N.Y. Konzentrierte waescheweichspuelmittel
US4424134A (en) * 1983-06-15 1984-01-03 The Procter & Gamble Company Aqueous fabric softening compositions
US4460485A (en) * 1983-07-15 1984-07-17 Lever Brothers Company Polyester fabric conditioning and whitening composition
DE3412090A1 (de) * 1984-03-31 1985-10-24 Henkel KGaA, 4000 Düsseldorf Verwendung von fettsaeure/hydroxyalkylpolyamin-kondensationsprodukten in fluessigen tensidhaltigen zusammensetzungen

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2391312A1 (fr) * 1977-05-16 1978-12-15 Basf Ag Plastifiant textile aqueux liquide

Also Published As

Publication number Publication date
FI80904B (fi) 1990-04-30
EP0199382A3 (en) 1987-12-02
FI861339A (fi) 1986-09-29
GB2174423A (en) 1986-11-05
KR860007416A (ko) 1986-10-13
IE860828L (en) 1986-09-28
DK139786A (da) 1986-09-29
IE58593B1 (en) 1993-10-20
FI80904C (fi) 1990-08-10
DK139786D0 (da) 1986-03-25
AU577009B2 (en) 1988-09-08
ATE53229T1 (de) 1990-06-15
EP0199382A2 (fr) 1986-10-29
SG49392G (en) 1992-06-12
HK48892A (en) 1992-07-10
CA1260654A (fr) 1989-09-26
FI861339A0 (fi) 1986-03-27
DE3671644D1 (de) 1990-07-05
GR860814B (en) 1986-07-21
MX162681A (es) 1991-06-17
KR930004515B1 (ko) 1993-05-27
JPS61275475A (ja) 1986-12-05
US4661269A (en) 1987-04-28
AU5535486A (en) 1986-10-02
GB8607692D0 (en) 1986-04-30
GB2174423B (en) 1989-06-28

Similar Documents

Publication Publication Date Title
EP0199382B1 (fr) Adoucissant liquide pour le linge
US4863620A (en) Acidic liquid fabric softener with yellow color that changes to blue upon dilution
US5183580A (en) Liquid fabric conditioner containing fabric softener and green colorant
US4855072A (en) Liquid fabric softener
US4994193A (en) Liquid fabric softener
EP1922397B1 (fr) Composition d'appret de tissus
US4822499A (en) Liquid fabric softener with stable non-staining pink color
US4897208A (en) Liquid fabric softener colored pink
JP3186808B2 (ja) 繊維製品柔軟剤及び赤色染料を含有する繊維製品用液体コンディショナー
US4844820A (en) Liquid fabric softener comprising light-unstable red dye in protective package
JP2551479B2 (ja) 布地コンディショニング組成物
NZ208745A (en) Liquid laundry detergent concentrate containing quarternary ammonium germicide
EP0315126A2 (fr) Compositions détergentes liquides ayant des propriétés de stabilité et d'adoucissement améliorées
US5151223A (en) Liquid softergent formulations having improved stability and softening properties
US6525016B2 (en) Blend of imidazolinium quat and amido amine quat for use in fabric softeners with premium softening, high-viscosity at low-solids and non-yellowing properties
US4976878A (en) Process for recovering gelled aqueous liquid fabric softener
EP0360331B1 (fr) Composition pour traiter le linge

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH DE FR GB IT LI NL SE

RBV Designated contracting states (corrected)

Designated state(s): AT BE CH DE FR IT LI NL SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH DE FR IT LI NL SE

17P Request for examination filed

Effective date: 19880511

17Q First examination report despatched

Effective date: 19890123

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE FR IT LI NL SE

REF Corresponds to:

Ref document number: 53229

Country of ref document: AT

Date of ref document: 19900615

Kind code of ref document: T

ITF It: translation for a ep patent filed

Owner name: ING. C. GREGORJ S.P.A.

REF Corresponds to:

Ref document number: 3671644

Country of ref document: DE

Date of ref document: 19900705

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

ITTA It: last paid annual fee
26N No opposition filed
EAL Se: european patent in force in sweden

Ref document number: 86200424.9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19950309

Year of fee payment: 10

Ref country code: DE

Payment date: 19950309

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 19950313

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19950315

Year of fee payment: 10

Ref country code: CH

Payment date: 19950315

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19950331

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19950428

Year of fee payment: 10

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AT

Effective date: 19960318

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19960319

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Effective date: 19960331

Ref country code: CH

Effective date: 19960331

Ref country code: BE

Effective date: 19960331

BERE Be: lapsed

Owner name: THE PROCTER & GAMBLE CY

Effective date: 19960331

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19961001

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19961129

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 19961001

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19961203

EUG Se: european patent has lapsed

Ref document number: 86200424.9

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050318